


Lord Have Mercy On My Rough and Rowdy Ways

by holyhael



Category: Supernatural
Genre: Alternate Universe, Anal Sex, Bondage, Breathplay, Daddy Kink, Dirty Talk, Dominant/Top Benny, Dominant/Top Castiel, Double Penetration, M/M, Makeup, Oral Sex, Orgasm Delay/Denial, Plot What Plot/Porn Without Plot, Porn, Rimming, Sex Toys, Spanking, Stockings, Submissive/Bottom Dean, Threesome - M/M/M
Language: English
Status: Completed
Published: 2013-08-30
Updated: 2013-08-30
Packaged: 2017-12-25 00:41:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,618
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/946635
Author URL: https://archiveofourown.org/users/holyhael/pseuds/holyhael
Summary: <blockquote class="userstuff">
              <p>Dean never thought he'd see Castiel again. He certainly never thought he'd be seeing him under these circumstances.</p>
            </blockquote>





	Lord Have Mercy On My Rough and Rowdy Ways

**Author's Note:**

> The title comes from a Head and the Heart song called [Down in the Valley](http://www.youtube.com/watch?v=2iSQGWpy0qY), which has nothing to do with the fic, really, but it stuck anyway.

The collar tied around Dean’s throat is made of rope. It sits substantially at the base of his throat and gives the illusion of not being able to breathe. Of course, Benny always makes sure it isn’t tied too tightly; he’s always ensuring Dean’s safety. One hand sneaks between his skin and the rope to test the space and finds it satisfactory. A wet kiss is sucked above the collar, the subtle scrape of teeth teasing Dean's sensitive skin.

"How much you think you can take tonight, brother?"

Fingers flirt around the edge of Dean's hole. Dean knows better than to thrust down on them, but the restraint is still hard to exercise. He grinds his teeth together.

"How much you askin'?" Dean counters. Ever since Dean expressed interest in bringing new players into their sex life, Benny has been enthusiastically searching for people to help him handle his sub. Sometimes Benny finds one perfect person, sometimes he finds several. Dean is eager for anything Benny allows him; he’ll take anything.

Benny smirks. "Got a friend lookin' for a good time. Just the one. Up for it?"

A shiver runs through Dean's body, and before he knows it, he's nodding and saying, "You know it," without a thought as to who Benny's talking about (though he thinks about Eli and Lenore and sort of hopes it’s either of them; they’re the first friends of Benny’s that come to mind that haven’t shared their bed, and Dean’s been looking forward to when that day comes). He trusts Benny like his own brother; Benny wouldn't bring another person into this unless he was sure about it, and if Benny's sure about it, Dean's sure about it. "Who is it?"

"Castiel Novak," Benny says. The familiar name curls too beautifully in his husky southern accent. "He’s a bit new and wants to be shown the ropes. Natural born dominant, that boy. You say yes?"

Dean only hesitates for a moment, and in that moment Benny extracts his fingers from Dean’s rim. There can only be one Castiel Novak in the world, in the state of Kansas, and that’s Castiel Novak, Dean’s college fling, the first man to make Dean whimper and cry at his feet, the first man Dean thinks he loved. It was a sad break up when Castiel wasn’t comfortable with Dean’s wishes to get rougher in the bedroom, but they parted on friendly enough terms, though they haven’t talked since. There have been times before he found Benny that Dean wished he could have gone back and just forget the flaws in their relationship.

“What is it, Dean?” Benny asks. “Somethin’ up?”

“I know him,” Dean admits. “Went out with him for a few months in college.”

“Oh.”

There’s only a hint of disappointment in Benny’s voice. Dean feels bad for turning down the offer to bring Castiel in their bedroom, so he says, “It wasn’t a bad breakup. He just wasn’t willing to do what I wanted him to do to me. What you do to me.”

Benny nods and considers for a moment. “Would you be comfortable bringing him in?”

There’s no hesitation when Dean says, “Yeah.”

“Bet I can have him here in the hour, is that okay?”

"Hell yes." Dean surges forward and pulls Benny's bottom lip into his mouth. The larger man's hands grab at Dean's jaw, fingers bruising into skin. “You’ll show him how a real dominant works,” Dean says. The thought of seeing Castiel again after all these years is spinning all sorts of ideas in his head. “What I really need. He’ll be jealous. He’ll want me back.”

“Well, he can’t have you,” Benny says. He grabs the collar possessively. “Not all of you.”

His thumb worms beneath the rope and presses down on the underside of his Adam’s apple. Dean’s mouth gapes open as he chokes. Just as he’s beginning to get lightheaded, Benny alleviates the press, smiles, and kisses the tip of Dean’s nose. Forehead to forehead, Benny’s eyes stare heavily right through Dean.

"Told 'im all about you," Benny says, voice like honey. His hand begins to travel down Dean’s body. "Bragged left and right about how I could make you tremble, how amazin' your pain threshold is. He won’t believe you’re the same animal he had back then. He’ll wish he could’ve been man enough too keep you. Glad it’s all worked in my favor.” He kisses Dean again, almost chastely for as quick as it ends. “Tell me how good daddy makes it.”

“Make it very good, daddy.” Dean gasps as Benny's fingers dig into him. Without lube, it burns, but Dean can take it. His eyes fall shut. “Very sweet. Daddy.”

“You tell Castiel that, ya hear? You show him just what he missed out on,” Benny commands, and Dean nods. “He don't believe me. Can't believe I snagged myself the best fish in the ocean. He tossed you right back in for me, didn’t he, though.”

“Tryin' to butter me up, daddy?” Dean asks a bit too cheekily.

Benny withdraws his finger to pinch Dean's ass. “Don't get like that now, boy,” he growls. He doesn't let go of his grip on Dean's cheek until he nods, and then he rubs the spot soothingly. “There's a good boy. You gonna be good tonight for daddy?”

Dean nods again. “I’ll be on my best behavior. Cross my heart.”

"Wouldn't expect anything less." His tone is gentler now as he continues to massage Dean's ass. "What say you we get a little prep done first? Think I'd like to see that plug in your tight little asshole. Show off how good a boy you are for me, wrapped in your ropes. You'd like that, boy?"

"You know best, daddy."

“Yes, but are you ready to be trussed up? You feel right?” Benny’s eyes search his face, looking for even a hint that Dean’s not game for what he has planned.

“Tie me up,” Dean pleads. He bats his eyes for good measure. “Please, daddy.”

Benny growls and kisses the last syllable out of Dean's mouth. "I’ll make ya nice and secure, promise, sweetheart." With one last kiss, he gently pushes Dean out of his lap so he can kneel at the bottom drawer of their dresser where they keep all their supplies. He comes back with rope in his hands and a glint in his eyes. “On your hands and knees, boy.”

Dean complies while Benny arranges rope. The first touch of the hemp is below his breasts. Benny gathers Dean’s arms gently behind his back so he can run the rope around his upper arms. Dean rests his cheek on the bed and tries to catch a glimpse of Benny over his shoulder as he snakes the rope around his neck and down to a V between his breasts so it can wrap around the rope already there. The rope makes several more crisscrosses before Benny finishes it off by wrapping Dean’s wrists to the knot at his back. A pentagram. It’s not so tight that it cuts off Dean’s circulation or can cause bruises, but it’s snug enough that if Dean so much as moves an inch it chafes against his skin. Benny strokes his hand down the rope and checks to make sure it isn’t too constricting.

“Like that, boy? So pretty for me. And we haven’t even gotten to the good stuff.”

Dean misses the hand when it’s gone, but Benny returns soon enough with a pair of lacy white stockings and a makeup kid. He rolls the hosiery up to Dean’s thighs, and even those small touches make Dean ache. His cock and balls hang heavy below him, and as Benny’s fingers draw closer to the intimate inside of his thigh, his cock twitches with want to be held and used.

“Such a pretty boy,” Benny purrs. His fingers delicately tickle Dean’s perineum, and Dean shuts his eyes against the urge to rut down and make the touch deeper to ease his want. Instead, Benny’s hand disappears entirely. The sound of a zipper being opened rips through the air. “Come on, doll. Open your pretty eyes.”

Benny is directly in front of him, kneeling on the side of the bed with the makeup bag in his hand. From it, he retrieves a wand of mascara. Dean is obediently still as it’s applied to his lashes, and he stays still for the eyeliner and eyeshadow as well. Blush is powdered onto his cheeks. The lipstick is painted on last, a subtle cherry number. When he’s finished his artwork, Benny sits back and admires Dean with the warmest expression. His large hand cups the side of Dean’s jaw, hot, steady, calloused. He kisses the tip of Dean’s nose.

“We’ve gotta stuff your ass,” Benny says. “Must be starvin’ for something to fill you up.”

“Want your cock,” Dean murmurs, though it’s useless. Benny sympathetically pets along his side.

“Not yet, boy, you know that.” Benny clicks his tongue and rises from the floor. He crouches at the dresser drawer again and paws through the ropes and silk. A triumphant cry precedes Benny’s return with a vibrator and its remote in one hand and a plug in the other. “Pick your poison, boy: the plug or the vibrator?”

The plug is small and silver with a green jewel flanged end - Benny says the color matches Dean’s eyes, and that's why he bought it. The vibrator is four inches or dark blue silicone, and it curves for perfect prostate stimulation. Its remote is wireless and allows whoever has it to control the toy’s pattern and intensity. Dean wouldn’t mind either of these toys in his ass, and he knows the decision is up to Benny, so he doesn’t say anything.

"'M thinkin' the vibrator." Benny purrs the last word, well aware of the effect he has on Dean with his voice alone. Benny could probably read him fucking terms and conditions and it'll get Dean hard. Dean’s always been attracted to men with voices like that. “Just to be nice.”

The plug is put away while the vibrator and remote are placed beside Dean on the mattress. When Benny sits back onto the bed, he has a bottle of lube and is applying it to his fingers. He drawls, "Let me stuff ya nice and pretty 'fore Castiel arrives. Oh, you’ll be achin’ by the time we’re ready for ya. There’s the ticket.” Benny's finger slips back into Dean's entrance, right where it belongs. Dean relaxes into the touch as more cool fingers prod at the outside of his rim. "Eager, boy?"

Dean nods, probably smearing his blush on the sheets. If Benny minds his artwork being messed up, he certainly doesn’t show it; his finger curls up and stokes against Dean’s prostate, and all Dean can do is gasp. The only thing preventing his release is his own self restraint, though the quality of that trait can get questionable in his and Benny’s bed. Benny’s just too good for him. The rope is unyielding as Dean’s arm attempts to reflex outward. “Oh, daddy.”

“You can come once before Castiel shows up,” Benny allows, and Dean lets out a breath of relief. “Only once if you think it’s necessary and that’s it. I don’t want you to be in too much pain. Think you can do it?”

"I can try and be a good boy," Dean murmurs. "You know me."

"There’s no tryin’ about it, boy," Benny growls harshly. His finger stops and almost punishingly yanks Dean’s entrance. “Another word like that and you’ll be lookin’ at my palm, right? No more lyin’. You know the rules.”

Chastised, Dean hides his face in shame. “Yes, daddy.”

“Good. Now.” Another finger slides in with the first, and Benny begins stretching him in earnest, scissoring his fingers, dipping them in and out as he pleases. "Think you're ready, boy? Can you take the fake cock?"

"Yes, daddy."

A kiss is pressed on the base of his shoulder blade; scruff scratches his back. Benny's free hand trails down Dean's side until it reaches his ass, and then he reaches over for the toy. The fingers inside of him withdraw. Dean tenses to prepare himself for the cool, unforgiving push of the vibrator. Benny must push a button on the remote control, because the otherwise silent room is suddenly full of buzzing. Though it's nowhere near Dean's ass at the moment, it's like he can already feel it outside of his entrance like lightning.

"Anticipation knottin' your spine? You can't wait to have something fill you, can't ya? Anything for that eager hole of yours. I can see you searchin' for it, boy. I ain't blind."

Blood rushes up to Dean's cheeks again and he stills. Benny chuckles and pets the small of his back lovingly. His hands are so warm, and Dean relaxes under them.

"I've worked ya too spoiled," Benny says.

"No, not yet, d-daddy." Dean can feel the vibrator closing in on his hole. Desire builds beneath Benny's steady hand and tightens his heavy balls. "Please, daddy, please."

"Oh, all right." There's a smile in Benny's words, Dean knows, and he turns his head to see it just when the vibrator first kisses his entrance. The flirting touch of it punches the breath out of Dean’s chest. His cock jerks. The vibrator pushes slowly and smoothly inside of him until it’s completely inside and shaking his ass, the flanged end sitting outside against his rim. Clever Benny kept the the toy from direct contact to his prostate, but every once and a while the pattern to the vibrations makes the tip graze that sweet spot that makes Dean’s blood yearn to sing, teasing him to frustration.

Dean groans and stays still while he completely adjusts to the intrusion. All the while, Benny sits behind him and pets his back, his side, down to his thigh and stopping just short of the lingerie. He doesn't move the toy again, but he does run a finger around the rim. Dean whimpers.

“Think of it,” Benny drawls in Dean’s ear. “The first thing Castiel’s gonna see when he enters the room is your pretty hole on display. Vibratin’, leakin’, _mine_.” A shudder that has nothing to do with the vibrator shakes Dean’s very core. His eyes are shut, but he knows Benny’s grinning.

"Get comfy, brother," Benny drawls. "I'm gonna go in the next room and call up Castiel. Remember: I’ve got the remote in my hands. You’re at my mercy, boy." Dean breathes deeply, in and out. "See you in an hour."

Dean presses his head into the mattress and grits his teeth against the urge to come. He can do this. He will do this.

The door closes with a soft click. The toy's vibrations suddenly intensify, making Dean moan into the mattress. He can’t tell if it’s his imagination or not when he hears the muffled sound of Benny’s chuckle. The vibrator calms back to its lowest and tamest setting, and Dean lets out a big breath. This is going to be a long hour, he can feel it.

+

To say it’s excruciating is an understatement. It seems like there’s nothing more in the world save for the vibrator in his ass, Benny in the next room, and Castiel who the fuck knows where. Thoughts come in short bursts of inspiration between the most brutal speeds. He thinks of Benny with his hand on the remote and a grin on his lips. He thinks of what Benny and Castiel are going to do to him and how helpless he’ll be to stop them. He thinks about meeting Castiel again for the first time in a nearly a decade, and the first thing Cas is going to see of him, just as Benny helpfully reminded him, is his hole, plugged up with a the fake cock and bound.

He does come once, and that release has long since dried up on the bed sheet. Dean doesn’t know how long ago he orgasmed, but he knows he’s rearing up for another one. He tries to get into a numbing headspace so he can zone out the rest of hour and forget the urge to come again, but just when he gets there the vibrations of the toy change and he squirms in place, fingernails scratching his back and teeth clenched into the bedsheets.

When the door creaks open again, it feels like days have gone by. Dean tries to raise his head, but he’s too weak as the speed changes yet again. His lungs shut down in his chest, and though Benny ensured the rope wouldn’t be too binding, suddenly it feels very tight and abrasive.

“He’s gorgeous,” a voice like aged whiskey says. Castiel. His voice has deepened considerably since they last talked. He’s always had a considerable tone, but now, its growl rivals Benny’s. Dean’s cock twitches feebly between his legs. He imagines he can feel Castiel’s penetrating gaze locking on that part of him and burning a hole through them. A drop of precome drips onto the puddle beneath him. Does Castiel recognize him like this? Does he recognize the constellation of freckles on Dean’s back? He should, having faced it plenty of times before. Dean wants to ask if Castiel knows it’s him, it’s Dean, but he doesn’t have control of his vocal chords.

“Told you.” Benny is smug. His palm cups around the heel of Dean’s foot, his fingers tickling along his arch through the hosiery. Dean squirms at the touch, but the ropes hold him still and his submissive position makes sure he has nowhere to go. A whimper crawls out of his teeth. “Been like this for an hour. Here, give it a press.”

Dean can guess Benny’s passed the remote over to Castiel, but that still doesn’t mean he’s ready as the low vibrations shoot up to their harshest level. He keens and buries his face in the mattress, driving his ass higher in the air, toes bunching the sheets. Through the blood in his ears and the buzzing, Dean can hear Castiel making a sound. It’s partly appreciative, partly wondrous. He can’t read the meaning of it if there’s a deeper one than getting hard.

“Wow.”

“Quite a catch, ain’t he?” Benny’s hand rings around Dean’s ankle. “Bet you feel bad about lettin’ him loose.” That answers Dean’s question, then. Castiel remains silent. “Looks like he’s ‘bout ready to play. What say you, boy? Ready to take cock again?”

Dean blinks through watery eyes to see Benny bent beside him. Desperate, he nods. “Hungry, daddy.”

“Smeared your makeup, boy.” A thumb wipes at the trail of mascara and eyeliner on Dean’s cheekbone; it comes away black. Benny’s expression is soft, caring, and loving as he asks, “Feelin’ good? Nothin’s too tight or nothin’?”

“No, daddy. Please, I’m ready. Daddy.”

“You scratched your back up good,” Benny observes. “Need something for that?”

Dean shakes his head.

He’s graced with a kiss on the forehead; it feels like benediction, cool and refreshing. Then, Benny stands back up and walks out of Dean’s line of sight.

“Your communication is remarkable,” Castiel comments.

“Key to everything, Castiel. ‘S how it’s done. If you and your partner can’t communicate, well, that ain’t no good. Communication and trust - very important.” Dean can hear the sound of clothes falling onto the floor. “Remember the word I told ya? If Dean says it, you back off immediately, no ifs, ands, or buts, capisce?”

“I capisce,” says Castiel.

“Good. Now come on. Put your hands on him.”

Dean braces for the feel of those hands on him again. They hesitantly touch on the wide lace of the stockings. It’s high enough that Dean feels his balls clench with anticipation. Fingers curl between the lace and Dean’s skin, tug the hosiery up.

“Don’t be afraid to touch him. He ain’t gonna bite ya, not unless you ask,” Benny says, and the fingers get bolder as they run further up and to the swell of his ass. Dean’s breath hitches. “Dean’s a greedy slut for touch, but you remember that, don’t ya?” Dean is pretty sure Castiel is glaring at Benny. The Castiel Dean remembers would be glaring, anyway. 

Castiel’s fingers cautiously touch the skin around the vibrator, causing Dean to shudder and push for more. Benny laughs. “Told you. See how greedy he is. Don’t matter that you’re not his daddy. He’ll get it from anywhere.”

“Can I?”

Dean feels fingers grip around the base of the toy, and after a moment they’re pulling the thing out. He is empty and loose and still shaking as if the toy never left him. Benny murmurs comforting words and strokes down his back.

“You’ll get your cock in a moment, boy,” Benny assures. “Which one does your greedy asshole want? Mine or Castiel’s?”

It’s his decision this time, Dean nows from Benny’s tone. His lungs heave as he tries to come up with an answer, but really he knows what he wants, just has to ask. He can ask. His chest tightens at the thought of being denied what he wants, but he knows it’s better to ask. Benny will want him to ask for it, to beg for it. He swallows the lump in his throat.

“I can take both of you,” he manages. “Both. Please, daddy. Need you both.”

Dean can practically feel their eyebrows shoot up. “Interestin’ choice, boy.”

It isn’t a no, not yet. He opens his eyes and searches for Benny’s husky frame in the blur of unshed tears. Desperation pitches his voice high and reedy. “Please, daddy. I’ve been a good boy. Please.”

He sees Benny exchange a glance with Castiel, who is just as Dean remembers him. Dark hair, hint of stubble, stoic. He’s naked at least from the waist up as far as Dean can see. There’s nothing in his expression that Dean can discern, but that may just be because of the blur.

“Cockslut,” Castiel growls. The word jerks Dean’s cock painfully, and Dean has to shut his eyes and try to hold back whatever noise his throat wants to let out.

Benny groans. “That’s the ticket.”

Emboldened, Castiel’s fingers hook around the knot of rope at Dean’s back. He pulls upward, lifting Dean’s face off the mattress. Dean can’t believe this is how Castiel is seeing him for the first time: face streaked with makeup, asshole open, arms bound behind his back, collar marking him as Benny's. His breath catches in his throat and comes out in a hiccup. He wants to weep for how much his balls ache to release again; instead, he’s forced to stare back into the thin iris of Castiel’s eye. Castiel’s definitely older, harshened by life. Nothing remains of the meek man who denied Dean’s desires all those years ago. Dean wonders for a fleeting moment where he went, but then Castiel yanks the ropes and jostles Dean back to attention.

“Have you thought about this, Dean?” Castiel snarls in his ear. “Have you been thinking about my cock?”

“‘Ve got Benny,” Dean chokes out.

“But that isn’t enough, is it, boy?” Castiel snarls, jerking the rope again and causing Dean to gasp. If Benny minds Castiel using his name for Dean, he doesn’t make it known. Dean wants to search for him, but he’s held by Castiel and unable to look away. “You’ve always needed more, more, more. There isn’t enough cock in the world to fill your appetite, is there?”

Dean swallows. If he didn’t know better, he would swear the creature whose dick was thick against his ass cheek was known by some other name than Castiel Novak. “You’re good enough. I’ll be good with you two.”

“Will you? Truly?”

When Dean doesn’t answer, Castiel releases the rope and lets him fall back onto the mattress with a thump. Dean lands on his cheek and the side of his nose, which aches from being smashed into the bed. He blinks his eyes back open to see Castiel’s heated stare turned Benny’s way. The soft slapping sound of jerking off hits Dean’s ears then, and he moves onto his other cheek to see Benny, naked and masturbating in front of them.

“Don’t mind me,” Benny says. “Y’all put on a good show.”

He releases his cock then and walks to the edge of the bed. Settling down, Benny reaches over and inserts one finger into Dean’s hole, still gaping from the grueling hour with the vibrator. Dean inhales sharply and tries to take Benny’s finger deeper, but Castiel stops him by pulling upward on his collar. It’s a light tug, but it’s enough to have Dean ceasing immediately.

“Hey, watch yourself, angel cake” Benny warns. The possessive tone in his voice fills Dean with glee. “Collar’s a thing. Shows he’s mine.”

“Bite me,” Castiel grinds out, and he tugs harder on the rope. This time Dean chokes, but he still feels so safe. Everything is still for a moment except for Dean’s breathing, and after a few tense heartbeats, Benny starts to move his fingers again.

“Just don’t choke ‘im too badly, else he’ll faint,” Benny cautions. His voice is still a little wary. Dean wonders why he’s letting Castiel touch his collar, but as Benny brushes against his prostate, he finds he doesn’t really care. “Little’s good, but not too much. Haven’t had an accident yet, and I don’t want to start now.”

“I understand,” Castiel says. One finger plucks off, though, and the minute pressure loosens slightly. “Do you think he can take both of our cocks?”

“You don’t have faith in my boy?” Benny asks incredulously. “He’ll do anything we ask him to. Can probably get him to take three if we said it’ll please us. Isn’t that right, boy?”

Dean murmurs a nonsensical yes into the mattress. Benny chuckles and rewards him by bending his knuckle and rubbing against his prostate again, this time firmer. His laughter grows when Dean writhes and chokes on Castiel’s hold on the collar. “Easy now, brother. Don’t want to hurt yourself.” With his free hand, Benny pets down Dean’s ass and the back of his thighs. “Your ass is too pretty to waste bein’ dead. I don’t think I’d be able to fuck a dead you, either. What good are you if you’re not beggin’ for me to let you come?”

“Not good,” Dean whimpers.

“What was that?” Benny asks.

He made an error, he knows. A chill that’s part eager anticipation and part dread rolls through him. When Dean refuses to repeat himself, the hand comes down. One hard slap strikes Dean’s ass cheek. He can tell the hand is wavering over his other cheek, because that’s how Benny works. Again, Benny asks, “What did you say to me, boy?”

Snot flows freely from Dean’s nose. He tries to sniff it up to no avail. “Nothing. Nevermind.”

The next strike smarts even more painfully than the last one, even though Dean is prepared for it. With the force of this spank, he goes forward and is choked by the collar even though Castiel does not move.

“Don’t lie to us, boy,” Castiel thunders. This time, it is Castiel’s doing that he can’t breathe. He tries to fill his lungs, but he is only allowed a thin reed of air. Castiel growls directly into his ear. “Tell your daddy the truth.”

Benny makes an appreciative sound behind them. Dean whimpers around the rope and tries to make out words, but none come. More tears gather and fall from his eyes. “S-sorry, d-d-daddy,” Dean blubbers. “I said - I said.” He sniffs. “Not good.”

The clout that hits his asshole rattles every bone in Dean’s body. A cry falls from Dean’s lips and he sobs for Benny to stop, but Benny’s not done. He hits again, a little less forcefully, but Dean still feels it with every cell in his body. The resulting stings almost make Dean forget the rope squeezing around his throat. His ass feels raw and painful, and it doesn’t help when Benny pinches the right cheek mercilessly.

“Remember what I said about that sorta talk, boy?” Benny asks, and Dean nods. “You need another spankin’ or d’you understand where you went wrong?”

“I understand,” Dean whimpers. The hold on his collar loosens but Castiel’s finger remains hooked under the rope.

“You’re a good boy, Dean,” Benny says, rubbing Dean’s tender ass cheeks. “Hate that I have to beat that into ya. You know that.”

Dean nods and sniffs again.

“He’s still self deprecating?” Castiel asks. There’s a disapproving frown in his voice, and Dean hates that he can tell that.

“‘Fraid so.” More lube is applied to his asshole, and it’s like a balm to his stinging flesh. Benny rubs it all around and stuffs it all into his hole. “He’s always been like that?”

Dean sees Castiel nod out of the corner of his eye. “Unfortunately.”

Benny grunts, clearly displeased, and pushes a third finger into Dean. It makes Dean feel better, so he breathes deep and lets go of the tension the spanking caused in him.

When Benny spreads his cheek, Dean doesn’t think much of it. But then, at the first touch of Benny’s tongue, Dean’s eyes fly open and his hips jerk in surprise, though Benny holds him in place. They haven’t done much of this before, but oh does it feel good, Benny’s beard tickling his skin. As Dean’s eyes focus, he realizes he’s looking at Castiel’s lap where his cock sits. The half-hard organ is practically begging for Dean to take it into his mouth, the slit staring right at him like Castiel used to, unwavering and fond but also a little exasperated. Dean’s hand lurches to hold it, but he’s still bound by the ropes; Castiel notices the diminutive twitch and he narrows his eyes.

“What is it, Dean?” Castiel asks.

“Your cock,” Dean says. He tears his eyes away from its appealing length to meet Castiel’s gaze. “I missed you cock, Cas. Really. Have thought about it.”

Castiel’s eyebrows raise. “Really?”

“Yes.” The simple word is punctuated by a gasp when Benny plunges his tongue into Dean’s hole, making the small licks from just moments ago seem like child’s play. Desperation turns Dean’s voice almost reedy. “Let me have you, Cas. Need you in my mouth. Please.”

Castiel’s eyes jump to Benny for approval. Benny must give his assent somehow, because Castiel jumps off the bed and pulls Dean to the edge so his head is half on the bed and half off. The mattress is high, so when Castiel stands beside Dean, his cock is at the perfect height for Dean to wrap his lips around. A moan escapes Castiel’s lips as Dean sucks a kiss onto the head; it swells in Dean’s mouth.

“Oh, Dean.” The fingers of Castiel’s right hand thread through Dean’s hair and hold him secure as he lavishes the cock head with his tongue; the other hand re-seizes the collar, cinching it tight against the back of Dean’s neck. “I can’t believe I forgot what your mouth feels like.” His eyes fall shut and his head tips back. Dean has a blazingly awesome fantasy of Benny bending over to press hickeys onto the bared column of Castiel’s throat, but Benny’s otherwise occupied licking open Dean’s entrance. Castiel’s two hands are opposites, one keeping him in place and the another urging him forward to suck as much of the proffered dick as he can. The feeling of Benny’s tongue in his ass and Castiel’s cock in his mouth is almost dizzying, but he holds onto reality. “Fuck, Dean,” Castiel wheezes. “Can you take all of it?”

In answer, Dean slides further down until his nose is tickled by Castiel’s hairs and the head of Castiel’s dick hits the back of his throat. The urge to swallow twitches his muscles, but he has no problem deepthroating, though his eyes begin to water some. Castiel hisses, and his hold on Dean’s hair stiffens. “Dean. Fuck.”

Benny pushes out of Dean’s hole. “Trained the gag reflex right out of ‘im. Nice, isn’t it?”

“Very,” Castiel exhales. He lets go of the collar to pet Dean’s throat, massaging the lump of dick in there. It makes Castiel moan loudly, lusciously, but he still pulls Dean away. “Your lipstick is smearing, boy.”

“Don’t care,” Dean tries to say, but it comes out mostly as incomprehensible garble. He itches to go up and down on Castiel’s cock in earnest, but Castiel keeps him in place at the head; he makes due instead with tonguing at the slit. The other man’s attention isn’t even fully on Dean anymore; it’s on Benny, who Dean can’t see, but he can guess what Benny’s doing. Taking a deep breath, Benny pushes his fat erection into Dean’s ass. Dean gasps at the first touch - Castiel inches inside of him further at the opportunity - then relaxes. “There’s a good boy,” Benny murmurs as Dean’s ass takes it, swallows him. Another whine is forced from Dean’s throat when Benny is completely buried in him; he can feel Benny’s balls below his asshole, just resting there.

“It’s a wonder you haven’t come yet again, boy,” Benny grunts. His thumbs massage the flesh of Dean’s cheeks. He doesn’t move otherwise, and it’s _agonizing_. “You’ve got your wish. You’ve got two fat cocks in ya. How’s it feel?”

Dean wants to cry from it all. He tries to tell them as much with his lips sheathing Castiel’s cock, but somehow he doesn’t think he gets his intent across.

“I don’t think he’s satisfied,” Castiel says. It doesn’t seem possible, but his voice is even rougher than before. Other than that, he sounds completely, amazingly composed. “Are you, Dean?”

He can’t answer. His eyes squeeze shut as Castiel’s grip tightens his scalp.

“No, he ain’t.” Benny’s gentle massage turns into a hard knead, almost like he’s trying to squeeze something out of Dean by pushing into his hips. Whether it’s words or come he’s looking for, Dean doesn’t know, but he wants to give both _so badly_. Benny hasn’t said anything about allowing Dean to orgasm a second time, and he can’t ask. “Get workin’ on that throat of his. He can take a bit of rough handling.”

“He won’t be able to speak when I’m done with him,” Castiel warns, sending a shiver down Dean’s spine. This is the Cas Dean wanted all those years ago. And finally he has him. His lips twitch to smile, but it’s impossible with Castiel’s girth.

“That’s the spirit.”

The hand was on Dean’s throat returns to his collar so Castiel can easier brutally pull Dean up and down his cock, lathering himself with Dean’s spit and lipstick. For his part, Dean is pliant, jaw unhinged. He tastes the salty substance of Castiel’s precome on his tongue (mixed in with the much less pleasant wax of the lipstick) before long, and he really wants to tell Castiel how much he’s missed that flavor.

Once Castiel’s worked a rhythm, Benny begins to move. Every time Castiel drags Dean away, Benny thrusts deep inside of him; and every time Benny nearly pulls out, Castiel’s cock hits the back of his throat. Dean feels like he’s on a sort of seesaw. He is numb and content. He can even forget how fucking heavy his balls are, how much he aches for release.

“Fuck, Dean, your perfect mouth.” Castiel pushes him off with a pop. A string of vaguely pink saliva and precome connects Dean’s mouth to Castiel’s erection. He stretches out his tongue to try and reclaim the cock, but Castiel holds him away while he pinches his root, breathing heavy. “Cockslut.”

“You ‘bout ready to join me?” Benny grunts. He jabs sharply into Dean’s prostate. Dean shows no restraint in shouting; the rope burns his arms as they attempt to fly out.

Castiel nods and steps away from Dean entirely. “How will it work?”

“We’ll work somethin’ out, right, boy?” Benny smacks Dean’s ass, which is still faintly stinging from the last time he was hit. With no one impeding his momentum, Dean jumps forward. His unloved cock swings sorely between his legs and bounces off his stomach.

“Right,” Dean croaks. He focuses on not releasing; he bites down on his lip until he’s sure he’s bleeding.

“Think I saw it like this in a video once,” Benny says, pulling out. A hollow feeling inside of Dean makes him want to simultaneously fill himself up and surrender into the mattress, admit defeat and let everything wash over him. None of these happen, though. He’s lifted up from the mattress by his bindings. On his knees, he trembles and shakes while Benny passes his grip to Castiel. “You hold him here while I get under and inside. Then you shove your cock in and we’ll see how much stuffin’ we can shove into this turkey.”

Benny has to widen Dean’s and Castiel’s knees as he situates himself beneath them. Dean sees Benny in all his glory: the stars in his eyes, the tan on his skin from work in the marina, his open mouth. He really wants to kiss Benny, transfer the salty taste of Castiel’s precome to him and smear whatever’s left of his lipstick on those lips, but Castiel holds him upright with just one hand, the other being busy worming its way where Benny’s dick had just exited. When it comes time to sink down onto his daddy’s cock, Benny and Castiel arrange and guide Dean to where he needs to be; Dean is far too oversensitive and weak to do more than just take everything and anything that’s handed to him, done to him. Benny’s cock slides back home beside Castiel’s fingers; the light burn at being stretched further than normal is soothed by Benny slicking up his fingers and lubricating Dean’s entrance even more.

“Your ass is gonna be sore for a week,” Benny says with a predatory grin. He gives an experimental thrust into Dean’s ass, and though it’s shallow, it packs a punch, especially with Dean’s current less than perfect equilibrium. Thankfully, Castiel’s hold prevents him from jacking up off of Benny entirely or falling off. “Not gonna be able to sit down unless it’s in my lap.”

Castiel’s lips attach to the side of Dean’s neck and slide down until the collar falls between his teeth. He tugs at the rope, and while Dean chokes and fights for breath, the bastard finds the wherewithal to rub his fingers up and down Benny’s cock, in and out of Dean’s ass. He’s a multitasking genius who’s even giving Benny’s impeccable levelheadedness a run for its money. Where was this man when they were dating, Dean wonders as yet another finger enters him, stretches him.

“Jesus, how many fingers do you have?” Dean asks, voice ruined and scratched. It feels like Castiel’s entire hand is snug beside Benny’s cock. He is so impossibly full; he has no idea how he’s going to be able to take Castiel’s dick as well as Benny’s, no matter how confident they are in his abilities or how eagerly he wants it.

"Just the eight," Castiel replies smoothly. "And currently only three are inside you."

Dean’s entire being feels like it’s made out of rubber: his stretched hole; his arms behind his back; his neck, unable to support his head anymore and falling forward. There’s a light touch on his oversensitive cock, Benny’s hardened fingers grazing beneath the head. It’s the first touch he’s had since the vibrator was shoved inside of him, and Dean responds by whining and trying to move into it, but his movement is minimal, laughable at best.

“God damn, boy, your cock’s about as purple as a plum,” Benny chuckles. He traces the thick veins, his touch always feather-light and agonizing.

“Daddy.” Dean’s voice breaks.

“I’m here for you, boy,” Benny says as Castiel’s fingers retreat. He thrusts up into Dean’s loose and aching ass without resistance. “It’s gonna to be all right, sugar.”

“I know,” he says. Benny’s comforting touches makes Dean feel like they’re wading in the calm waters before the storm. It’s a safe, loving harbor where Benny pets along his side and he continually checks and tests Dean’s bindings.

“They’re still okay?” Benny asks, trailing his hand along the pentagram on Dean’s chest.

Dean manages a weak nod. He hears the wet sound of lube being applied, presumably to Castiel’s erection. The sound makes his cock twitch eagerly, painfully. Benny takes notice; he cups a large hand around Dean’s cock to gives it a few jerks.

“It’s too painful?” Benny asks next.

“I want to come,” Dean whines pathetically. His eyes prick with tears that make Benny a blurry sketch of tanned skin and dark hair against a cool blue background.

“I got faith you can last for a little while longer,” says Benny, giving one last buck up before the cool demand of Castiel’s well-lubricated dick pushes beside him and into Dean. Dean takes in a sharp breath, eyes flying wide open, jaw dropping. His expression soon turns to a slight grimace as Castiel forces himself inside; no matter how much lube he used or how well he prepped Dean, it still burns like Hell to have so much inside of him. Benny remains still while Castiel slides himself as deep as he can go, which takes a good amount of grunting and repositioning on Castiel’s part. Dean tries to be attentive to where Castiel and Benny need him, but he realizes that he isn’t much good for anything right now except to be a hole to be fucked into and that he doesn’t have very good maneuverability anyway, legs like jelly and arms held secure behind him. So he attempts to draw in as much breath as he can and keep loose to give Castiel room.

It seems to take forever, but at last Castiel stops, chest now flush against Dean’s back, his arm now wrapped around Dean’s torso to hold him up. Dean can feel Castiel’s hot breath shuddering against the curve of his neck, and he can hear the pleased sounds Benny’s drawing out.

“This is amazin’, boy,” Benny says with his head fallen on the mattress and his eyes closed. Blindly, one hand reaches to pump Dean’s cock. “I’m so proud of you,”

It’s a wonder that there’s any blood to spare from his dick to allow Dean to blush. Benny sweeps a thumb over his slit to spread his precome around. “I truly am, brother. Lookit you, taking two cocks at once.” Through his tears, Dean thinks he sees Benny grin at him. “Not everybody can do what you’re doin’. I’m proud to call you my boy.”

At least one tear drops off Dean’s cheek and onto Benny’s abdomen to be soaked up in his hair. Dean sniffs his snot up into his nose so that doesn’t fall as well. Benny’s large hand comes up to caress his cheek and wipe the damp trail beneath his eyes.

“Are you okay, Dean?” Castiel’s voice curls in his ear, and Dean nods.

“‘M fine,” he sniffs. He doesn’t even know how to explain what’s going on inside of him to Benny, who he’s been with for the past two years, let alone to Castiel as well, who he hasn’t seen since they broke up almost a decade ago.

“We can stop,” Castiel says, leaning his hips back and dragging his cock  backwards against Benny’s erection and the muscle of Dean’s ass. The movement, though cursory, shocks both Dean and Benny, though Benny probably more than Dean given how loudly he inhales. Castiel stops again, waiting.

“No, no,” Dean finally manages after a few tense, still moments. His voice is broken.

“Give ‘im all ya got, Castiel,” Benny says. He winds his arms around Dean’s body to spread his asscheeks even wider. Dean is caught in a cage made of the two most awesome bodies in the world, and it is like Heaven. “He can take it, cain’t ya, boy?”

“I can,” says Dean. “I’m a good boy.”

Dean thinks that if Benny could, he’d be kissing his smile onto Dean’s lips in a heartbeat. “Yes you are. Go on, Castiel. Give ‘im Hell.”

Experimentally, Castiel pushes himself back fully inside. There is less burn in the thrust than the first one, though there is still some that Dean relishes. The next push in and out is even easier, and soon Castiel builds himself a rhythm that fucks with careful and tentative instead of cuddling them. None of the memories of the Castiel of a decade ago match with this beast. What changed Castiel in their time apart, Dean’s mind is on the brink of wondering, but the pace Castiel sets doesn’t allow coherent thought process.

There isn’t any room in Dean’s ass for his prostate not to be stimulated constantly. It’s amazing that he hasn’t come yet; Benny must be so proud of his self restraint. Each thrust of Castiel’s just punishes him further and makes it harder to hold his orgasm at bay. There is no relief in sight. New tears fall onto Benny’s chest hair.

“You look like you need to come,” Benny notices. He brushes away a tear that hasn’t fallen from Dean’s cheek. “It’s okay, boy. You can.”

With permission, Dean lets it all go. He tenses up and explodes in a ball of pure, shining ecstasy. The explosion blows away his mind to clear a spot for blinding white field where the sun is warm on his skin and there’s an eternal high intoxicating the air. When the feeling begins to fade and Dean comes back to himself, he realizes that Castiel is still fucking him and that his hole is wetter. Benny came as well, just like he likes to: in sync with Dean. He peels open his eyes to see that his come has landed all over Benny’s torso, a splash or two even making it to his face and neck. Benny is still stroking him, though there is little left to be milked from him.

“Was that good, boy?” Benny asks with a grin, and Dean nods with the beginning of his own smile on his lips. His limbs feel soft. “You got me dirty.”

“Sorry,” Dean says, though it’s hard to be, because Benny looks good painted in white, and Dean’s going to have to lick every trace of semen from him. A last, electric thrill makes his weakening dick want to get interested again at the thought of eating his own seed out of the thick forest of Benny’s chest hair.

“You’re going to have to clean that up, Dean,” Castiel growls into his ear.

“It’s like you’re readin’ our minds,” Benny says. “C’mon, now. It’s gonna dry and it won’t be no good like that.”

“You need more,” Castiel determines after a moment.

He pulls out of Dean with a wet sound. Dean feels empty and vulnerable without his presence, though Benny’s cock is still burrowed inside of him. Once it’s determined that Dean can’t stay up by himself, Benny holds Dean steady by the elbows while Castiel comes around to the side, cock in hand and eyes dark. After a few pulls, Castiel comes across Benny’s stomach as well. Dean wonders, since his precome does, if his come tastes the same as it did ten years ago. Castiel’s orgasm face certainly looks the same: mouth open, eyelids tight over his eyes, eyebrows shooting up. His chest heaves in an out as he finishes with the last drops of his come falling out over Benny’s nipple.

“There you have it,” Castiel says, voice ragged and breathy. “Eat.”

The words, again, go straight to his dick, though it’s very much down for the count. Benny hefts him off of his cock so he can reach it all, and suddenly Dean is entirely empty. He feels Benny’s come and the lube dripping from his open, sloppy hole, down his thigh, and onto his stockings or the bedsheets.

Since he still doesn’t have use of his arms, Dean is lowered to Benny’s torso with Castiel’s help. The first taste he catches on his tongue is Benny’s sweat, but as he travels up, the even saltier tang of Castiel’s come touches his taste buds and he moans.

“That’s right, boy. Go on, lick it up before it dries up.”

With Benny’s encouragement, Dean wastes no time tonguing Benny’s entire chest to swipe up the delicious come. He’s impartial to his own seed, but when he recognizes Castiel’s on his tongue, he pays special attention to make sure he gets every last drop in that spot.

When he collects the last drop from Benny’s cheek and it’s all gone, Dean wants to whine a little and see if he can tug on either Benny’s or Castiel’s dick to see if more come will come out, or if it’s worth it to lick what fell out of his ass from the bed sheets, but a massive yawn pops his jaw, and Benny chuckles at him.

“Looks like someone’s ready for bed, huh?” Benny says. He brings Dean, pliant, into his arms, and Dean completely falls into his chest, his magnetic heat cradling him. When Benny’s lips meet his, Dean wonders if he can taste the come in his mouth or if he swallowed it thoroughly enough. “Let’s get you out of this, what ‘ja say?”

Dean knows the ropes have to come off, but he still wishes he could wear them forever. Maybe he can ask Benny to dress him up tightly in them one day before they go out. Perhaps not as binding as what he’s wearing now, but something still similar that marks Dean as Benny’s, even if no one sees it. He nods, and both Benny and Castiel start to work on loosening the tie so Dean can be freed. His wrists are untied first, so he can bend his elbows again and drop his arms. Though he was never in danger of losing circulation, blood rushes into his arms. The ropes are then unwound from his chest. Throughout the entire process, Benny kisses the light line where the rope sat on Dean’s skin, and eventually Castiel catches up on the ritual as well. Benny also makes sure to tell Dean how great he is and how proud of him he is. Once the ropes are discarded to the side, Benny wraps Dean up completely in his arms and tenderly kisses his neck, but when another yawn opens Dean’s jaw, Benny pulls back and chuckles again.

“Dean’s getting a mite sleepy,” Benny says amusedly, which is an understatement, and Dean would say so but he’s too exhausted to make his mouth move. Silence permeates the air, in which Dean imagines Benny and Castiel staring at each other. “You’re welcome to join us if you want. Dean’s still very much the cuddler.”

“Would that be okay?”

Benny nods. “More than okay, really. Dean should get all the love he can right now. It’s important so he doesn’t drop too much later on. What d’you say?”

The next thing Dean knows, he is being pulled to lay down on the bed, and he is covered by a heavy blanket. The mattress shifts. Two separate heat sources crowd on either side of him. He falls asleep with two arms draped over his waist and hips. It’s such a nice place to fall asleep.


End file.
